CHEBI:16977 - L-alanine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name L-alanine
ChEBI ID CHEBI:16977
ChEBI ASCII Name L-alanine
Definition The L-enantiomer of alanine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6171, CHEBI:40734, CHEBI:40735, CHEBI:46308, CHEBI:13069, CHEBI:21216
Supplier Information ChemicalBook:CB4350297, eMolecules:476060, ZINC000004658553
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Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a non-polar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH+3) and its carboxyl group deprotonated (as −CO−2). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG). The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins. The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls: 131  (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte.
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Formula C3H7NO2
Net Charge 0
Average Mass 89.09322
Monoisotopic Mass 89.04768
InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
InChIKey QNAYBMKLOCPYGJ-REOHCLBHSA-N
SMILES C[C@H](N)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Arabidopsis thaliana (NCBI:txid3702) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor
An EC 4.3.1.* (ammonia-lyase) inhibitor that interferes with the action of diaminopropionate ammonia-lyase (EC 4.3.1.15).
fundamental metabolite
Any metabolite produced by all living cells.
(via alanine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-alanine (CHEBI:16977) has role EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor (CHEBI:77881)
L-alanine (CHEBI:16977) has role fundamental metabolite (CHEBI:78675)
L-alanine (CHEBI:16977) is a L-α-amino acid (CHEBI:15705)
L-alanine (CHEBI:16977) is a alanine (CHEBI:16449)
L-alanine (CHEBI:16977) is a proteinogenic amino acid (CHEBI:83813)
L-alanine (CHEBI:16977) is a pyruvate family amino acid (CHEBI:26463)
L-alanine (CHEBI:16977) is conjugate acid of L-alaninate (CHEBI:32431)
L-alanine (CHEBI:16977) is conjugate base of L-alaninium (CHEBI:32432)
L-alanine (CHEBI:16977) is enantiomer of D-alanine (CHEBI:15570)
L-alanine (CHEBI:16977) is tautomer of L-alanine zwitterion (CHEBI:57972)
Incoming (+)-(S)-alapyridaine (CHEBI:76046) has functional parent L-alanine (CHEBI:16977)
2-L-alanyl-5-tert-butyl-1,3,4-oxadiazole (CHEBI:40893) has functional parent L-alanine (CHEBI:16977)
L-alanine derivative (CHEBI:83943) has functional parent L-alanine (CHEBI:16977)
L-alanyl-L-alanine (CHEBI:72816) has functional parent L-alanine (CHEBI:16977)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Ala (CHEBI:73313) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Asp (CHEBI:73317) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Asp-Asp (CHEBI:73314) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Gly (CHEBI:73318) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Pro (CHEBI:73323) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Pro-Pro (CHEBI:73324) has functional parent L-alanine (CHEBI:16977)
Ala-Ala-Ser (CHEBI:73321) has functional parent L-alanine (CHEBI:16977)
Ala-Arg (CHEBI:137238) has functional parent L-alanine (CHEBI:16977)
Ala-Asn (CHEBI:73330) has functional parent L-alanine (CHEBI:16977)
Ala-Asn-Asn-Pro (CHEBI:73326) has functional parent L-alanine (CHEBI:16977)
Ala-Asn-Asp-Pro (CHEBI:73329) has functional parent L-alanine (CHEBI:16977)
Ala-Asn-Gln-Ser (CHEBI:73331) has functional parent L-alanine (CHEBI:16977)
Ala-Asp-Gly (CHEBI:73341) has functional parent L-alanine (CHEBI:16977)
Ala-Asp-Pro (CHEBI:73342) has functional parent L-alanine (CHEBI:16977)
Ala-Asp-Ser (CHEBI:73344) has functional parent L-alanine (CHEBI:16977)
Ala-Cys (CHEBI:157787) has functional parent L-alanine (CHEBI:16977)
Ala-Cys-Gly (CHEBI:73345) has functional parent L-alanine (CHEBI:16977)
Ala-Gln-Pro (CHEBI:73347) has functional parent L-alanine (CHEBI:16977)
Ala-Gly-Ala-Gly (CHEBI:143968) has functional parent L-alanine (CHEBI:16977)
Ala-Gly-His (CHEBI:73348) has functional parent L-alanine (CHEBI:16977)
Ala-Gly-Pro (CHEBI:73349) has functional parent L-alanine (CHEBI:16977)
Ala-Gly-Ser (CHEBI:73350) has functional parent L-alanine (CHEBI:16977)
Ala-Gly-Tyr (CHEBI:73351) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Ala (CHEBI:158283) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Ala-Pro (CHEBI:73353) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Asp-Asp (CHEBI:73355) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Asp-Gly (CHEBI:73362) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Leu-Asp (CHEBI:73363) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Leu-His (CHEBI:73365) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Leu-Ser (CHEBI:73366) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Leu-Thr (CHEBI:73368) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Thr-Gln (CHEBI:73372) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Thr-Pro (CHEBI:73292) has functional parent L-alanine (CHEBI:16977)
Ala-Leu-Val-Ser (CHEBI:73375) has functional parent L-alanine (CHEBI:16977)
Ala-Met-Asp-Tyr (CHEBI:176849) has functional parent L-alanine (CHEBI:16977)
Ala-Met-Gln-Gln (CHEBI:137239) has functional parent L-alanine (CHEBI:16977)
Ala-Met-Ser-Arg (CHEBI:73376) has functional parent L-alanine (CHEBI:16977)
Ala-Phe-Thr-Ser (CHEBI:73377) has functional parent L-alanine (CHEBI:16977)
Ala-Phe-Trp-Asn (CHEBI:73379) has functional parent L-alanine (CHEBI:16977)
Ala-Pro (CHEBI:73393) has functional parent L-alanine (CHEBI:16977)
Ala-Ser (CHEBI:73394) has functional parent L-alanine (CHEBI:16977)
Ala-Thr-Ala-Pro (CHEBI:73381) has functional parent L-alanine (CHEBI:16977)
Ala-Trp-Asn-Asp (CHEBI:73382) has functional parent L-alanine (CHEBI:16977)
Ala-Tyr (CHEBI:73395) has functional parent L-alanine (CHEBI:16977)
Ala-Val-Asp-His (CHEBI:73383) has functional parent L-alanine (CHEBI:16977)
Ala-Val-Asp-Pro (CHEBI:73384) has functional parent L-alanine (CHEBI:16977)
Ala-Val-Asp-Ser (CHEBI:73386) has functional parent L-alanine (CHEBI:16977)
Ala-Val-Asp-Tyr (CHEBI:73391) has functional parent L-alanine (CHEBI:16977)
Ala-Val-Pro-Pro (CHEBI:73392) has functional parent L-alanine (CHEBI:16977)
Glu-Ala-Trp (CHEBI:73490) has functional parent L-alanine (CHEBI:16977)
Glu-Leu-Phe-Ala (CHEBI:73485) has functional parent L-alanine (CHEBI:16977)
Glu-Lys-Trp-Ala (CHEBI:73487) has functional parent L-alanine (CHEBI:16977)
Gly-Ala-Ala (CHEBI:144460) has functional parent L-alanine (CHEBI:16977)
L-Alanine-d3 (CHEBI:229589) has functional parent L-alanine (CHEBI:16977)
Leu-Ala (CHEBI:73527) has functional parent L-alanine (CHEBI:16977)
Leu-Ala-Asp (CHEBI:73524) has functional parent L-alanine (CHEBI:16977)
Leu-Ala-Gly (CHEBI:73526) has functional parent L-alanine (CHEBI:16977)
Leu-Ala-Ser (CHEBI:73525) has functional parent L-alanine (CHEBI:16977)
Leu-Leu-Ala (CHEBI:73565) has functional parent L-alanine (CHEBI:16977)
Leu-Thr-Ala (CHEBI:73572) has functional parent L-alanine (CHEBI:16977)
Lys-Ala (CHEBI:61872) has functional parent L-alanine (CHEBI:16977)
Met-Ala (CHEBI:73610) has functional parent L-alanine (CHEBI:16977)
Met-Ala-Asp (CHEBI:73609) has functional parent L-alanine (CHEBI:16977)
Met-Ala-Met (CHEBI:140747) has functional parent L-alanine (CHEBI:16977)
methyl-L-alanine (CHEBI:25264) has functional parent L-alanine (CHEBI:16977)
norophthalmic acid (CHEBI:143251) has functional parent L-alanine (CHEBI:16977)
Phe-Ala (CHEBI:73630) has functional parent L-alanine (CHEBI:16977)
Phe-Ala-Asp (CHEBI:73627) has functional parent L-alanine (CHEBI:16977)
Phe-Ala-Gly (CHEBI:73628) has functional parent L-alanine (CHEBI:16977)
Phe-Ala-Pro (CHEBI:73617) has functional parent L-alanine (CHEBI:16977)
Phe-Trp-Ala (CHEBI:73640) has functional parent L-alanine (CHEBI:16977)
Thr-Ala-Ala (CHEBI:73654) has functional parent L-alanine (CHEBI:16977)
Thr-Ala-Asp (CHEBI:73655) has functional parent L-alanine (CHEBI:16977)
Thr-Ala-His (CHEBI:73656) has functional parent L-alanine (CHEBI:16977)
Thr-Ala-Ser (CHEBI:73657) has functional parent L-alanine (CHEBI:16977)
Trp-Ala (CHEBI:73710) has functional parent L-alanine (CHEBI:16977)
Trp-Ala-Asp (CHEBI:73671) has functional parent L-alanine (CHEBI:16977)
Trp-Ala-Gly (CHEBI:73691) has functional parent L-alanine (CHEBI:16977)
L-alaninium (CHEBI:32432) is conjugate acid of L-alanine (CHEBI:16977)
L-alaninate (CHEBI:32431) is conjugate base of L-alanine (CHEBI:16977)
D-alanine (CHEBI:15570) is enantiomer of L-alanine (CHEBI:16977)
L-alanine residue (CHEBI:46217) is substituent group from L-alanine (CHEBI:16977)
L-alanino group (CHEBI:32434) is substituent group from L-alanine (CHEBI:16977)
L-alanyl group (CHEBI:32433) is substituent group from L-alanine (CHEBI:16977)
L-alanine zwitterion (CHEBI:57972) is tautomer of L-alanine (CHEBI:16977)
IUPAC Name
L-alanine
Synonyms Sources
(2S)-2-aminopropanoic acid IUPAC
(S)-2-aminopropanoic acid ChEBI
(S)-alanine NIST Chemistry WebBook
A ChEBI
Ala NIST Chemistry WebBook
ALANINE PDBeChem
L-2-Aminopropionic acid KEGG COMPOUND
L-Alanin ChEBI
L-Alanine KEGG COMPOUND
L-alpha-Alanine KEGG COMPOUND
L-α-alanine NIST Chemistry WebBook
Manual Xrefs Databases
4255 DrugCentral
ALA_LFOH PDBeChem
Alanine Wikipedia
ALPHA-ALANINE MetaCyc
C00001332 KNApSAcK
C00041 KEGG COMPOUND
D00012 KEGG DRUG
DB00160 DrugBank
ECMDB00161 ECMDB
HMDB0000161 HMDB
YMDB00154 YMDB
View more database links
Registry Numbers Types Sources
1720248 Reaxys Registry Number Reaxys
49628 Gmelin Registry Number Gmelin
56-41-7 CAS Registry Number KEGG COMPOUND
56-41-7 CAS Registry Number ChemIDplus
56-41-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
11 April 2024